Question 1

Explain why the synthetic route shown below would be unsuccessful.

Accepted Answer

The tertiary bromide is too hi

Question 2

Provide an acceptable name for the compound below.

Accepted Answer

4-bromo-2-

Question 3

Provide the structure of the major organic product in the reaction shown below.

Accepted Answer

The answer of Provide the structure of the major organic...

Question 4

Provide the major organic product(s) of the reaction below.

Accepted Answer

The answer of Provide the major organic product(s) of the...

Question 5

How would one used a Grignard-based synthesis to accomplish the following transformation?
methyl isobutyrate [(CH3)2CHCO2CH3] to 3-ethyl-2-methylpentan-3-ol

Accepted Answer

1. CH₃CH₂MgB

Question 6

Provide the structure of the major organic product in the reaction below.

Accepted Answer

The answer of Provide the structure of the major organic...

Question 7

Which is the stronger acid, phenol or 4-nitrophenol?

Accepted Answer

The answer of Which is the stronger acid, phenol or...

Question 8

Provide the reagents necessary to accomplish the following transformation.
methyl benzoate (PhCO2CH3) to benzyl alcohol (PhCH2OH)

Accepted Answer

Question 9

Provide the major organic product(s) of the reaction below.

Accepted Answer

The answer of Provide the major organic product(s) of the...

Question 10

The reaction of CH3CH2MgBr with CH3COCH2CH3 gives:

Accepted Answer

A)  an achiral product. 
B)  a mixture of diastereomers. 
C)  the racemate of a chiral product. 
D)  a single enantiomer. 
E)  none of the above 
A)  an achiral product. 
B)  a mixture of diastereomers. 
C)  the racemate of a chiral product. 
D)  a single enantiomer. 
E)  none of the above

Question 11

Provide the structure of the major organic product in the reaction shown below.

Accepted Answer

The answer of Provide the structure of the major organic...

Question 12

Provide a detailed step-by-step mechanism that would account for the formation of the product in the following reaction.

Accepted Answer

The answer of Provide a detailed step-by-step mechanism that would...

Question 13

What is synthesis gas and what commercially important alcohol is prepared from it?

Accepted Answer

Synthesis gas is a mixture of

Question 14

Which of the following reactions will result in the formation of a secondary alcohol(s) in good yield?

Accepted Answer

A) 
  
B) 
  
C) 
  
D) 
  
E)  both A and D 
A) 
  
B) 
  
C) 
  
D) 
  
E)  both A and D

Question 15

Provide the reagents necessary to accomplish the following transformation.

Accepted Answer

The answer of Provide the reagents necessary to accomplish the...

Question 16

When a ketone is treated with LiAlH4 followed by addition of H2O, what general class of product results?

Accepted Answer

A)  primary alcohol 
B)  secondary alcohol 
C)  tertiary alcohol 
D)  ether 
E)  aldehyde 
A)  primary alcohol 
B)  secondary alcohol 
C)  tertiary alcohol 
D)  ether 
E)  aldehyde

Question 17

What reagent(s) are needed to complete the following reaction?

Accepted Answer

A)  1) LiAlH4, 2) H3O+ 
B)  1) NaBH4, 2) H3O+ 
C)  H2, Pd 
D)  1) DIBAL-H, 2) H3O+ 
A)  1) LiAlH4, 2) H3O+ 
B)  1) NaBH4, 2) H3O+ 
C)  H2, Pd 
D)  1) DIBAL-H, 2) H3O+

Question 18

1-Methylcyclopentanol is classified as ________.

Accepted Answer

A)  a primary alcohol 
B)  a secondary alcohol 
C)  a tertiary alcohol 
D)  a phenol 
E)  an enol 
A)  a primary alcohol 
B)  a secondary alcohol 
C)  a tertiary alcohol 
D)  a phenol 
E)  an enol

Question 19

Which of the following alkyl halides would be suitable to use when forming a Grignard reagent?

Accepted Answer

A)  BrCH2CH2CH2CN 
B)  CH3COCH2CH2Br 
C)  (CH3)2NCH2CH2Br 
D)  H2NCH2CH2Br 
E)  all of the above 
A)  BrCH2CH2CH2CN 
B)  CH3COCH2CH2Br 
C)  (CH3)2NCH2CH2Br 
D)  H2NCH2CH2Br 
E)  all of the above

Question 20

Provide the major organic product of the reaction below.

Accepted Answer

The answer of Provide the major organic product of the...

Exam 10: Structure and Synthesis of Alcohols

Explain why the synthetic route shown below would be unsuccessful.

Provide an acceptable name for the compound below.

Provide the structure of the major organic product in the reaction shown below.

Provide the major organic product(s) of the reaction below.

How would one used a Grignard-based synthesis to accomplish the following transformation? methyl isobutyrate [(CH3)2CHCO2CH3] to 3-ethyl-2-methylpentan-3-ol

Provide the structure of the major organic product in the reaction below.

Which is the stronger acid, phenol or 4-nitrophenol?

Provide the reagents necessary to accomplish the following transformation. methyl benzoate (PhCO2CH3) to benzyl alcohol (PhCH2OH)

Provide the major organic product(s) of the reaction below.

The reaction of CH3CH2MgBr with CH3COCH2CH3 gives:

Provide the structure of the major organic product in the reaction shown below.

Provide a detailed step-by-step mechanism that would account for the formation of the product in the following reaction.

What is synthesis gas and what commercially important alcohol is prepared from it?

Which of the following reactions will result in the formation of a secondary alcohol(s) in good yield?

Provide the reagents necessary to accomplish the following transformation.

When a ketone is treated with LiAlH4 followed by addition of H2O, what general class of product results?

What reagent(s) are needed to complete the following reaction?

1-Methylcyclopentanol is classified as ________.

Which of the following alkyl halides would be suitable to use when forming a Grignard reagent?

Provide the major organic product of the reaction below.

Introduction and Review

Structure and Properties of Organic Molecules

Structure and Stereochemistry of Alkanes

The Study of Chemical Reactions

Stereochemistry

Alkyl Halides: Nucleophilic Substitution and Elimination

Structure and Synthesis of Alkenes

Reactions of Alkenes

Alkynes

Reactions of Alcohols

Infrared Spectroscopy and Mass Spectrometry

Nuclear Magnetic Resonance Spectroscopy

Ethers, Epoxides, and Thioethers

Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy

Aromatic Compounds

Reactions of Aromatic Compounds

Ketones and Aldehydes

Amines

Carboxylic Acids

Carboxylic Acid Derivatives

Condensations and Alpha Substitutions of Carboxyl Compounds

Carbohydrates and Nucleic Acids

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

Filters

How would one used a Grignard-based synthesis to accomplish the following transformation? methyl isobutyrate [(CH₃)₂CHCO₂CH₃] to 3-ethyl-2-methylpentan-3-ol

Provide the reagents necessary to accomplish the following transformation. methyl benzoate (PhCO₂CH₃) to benzyl alcohol (PhCH₂OH)

The reaction of CH₃CH₂MgBr with CH₃COCH₂CH₃ gives:

When a ketone is treated with LiAlH₄ followed by addition of H₂O, what general class of product results?